Rivaroxaban, also known as 5-chloro-N-[2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5(S)-ylmethyl]thiophene-2-carboxamide, acts by inhibition of the active form of coagulation factor Xa.
Rivaroxaban is currently in clinical trials for pulmonary embolism, stroke, thromboembolism, deep venous thrombosis, thrombosis, and acute coronary syndrome (http://clinicaltrials.gov/).
Rivaroxaban is converted to two major metabolites in vivo, the CYP3A4 mediated product of morpholinone ring oxidation (M1), and the product of chlorothiophenyl amide hydrolysis and subsequent glycine conjugation (M4). Neither metabolite is active. (Weinz, C et al., Drug Metab Rev, 2004, 36 (suppl 1): 98).
Adverse events associated with the use of rivaroxaban include, but are not limited to, ageusia (loss of taste), ecchymosis (bruising) and headache (Kubitza, D et al., Cl Pharmacol Therapeutics, 2005, 78 (4): 412-421).
Despite the beneficial activities of rivaroxaban, there is a continuing need for new compounds for treating the aforementioned diseases and conditions.